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Strategic Communications Advisory For Visionary Founders
Actionable
Takeaways
Choose your investors and board strategically:
Charlotte learned the importance of building a supportive board that acts as true partners. As she noted, "You really need to find people who want to be on a team with you when it comes to a board and investors and in the trenches." Founders should carefully evaluate potential investors beyond just capital, looking for those who will provide meaningful support during challenging times.
Trust your instincts on pivots:
When market conditions change, founders need to be willing to evolve their product strategy. Charlotte explained, "Where there's a will, there's a way... If your product isn't perfectly aligned to what the market needs, you pivot." The key is balancing quick decisions in urgent situations while taking time for careful consideration when possible.
Rethink traditional enterprise marketing:
Cold outreach and demand generation may not be effective for enterprise sales in today's environment. Inclusively found success by systematically leveraging investor and customer networks, with Charlotte sharing, "We tripled our weekly meeting rates" after implementing a structured approach to warm introductions through investors.
Build product with enterprise design partners:
When pivoting their product strategy, Inclusively worked closely with Salesforce as their first pilot customer. Charlotte emphasized the value of "interviewing them, having them help us build this product" to ensure market fit. Founders should seek out and deeply engage with marquee customers who can help shape and validate new solutions.
Align marketing with customer success:
For enterprise companies, Charlotte recommends closely integrating marketing with the teams delivering customer value. This ensures marketing messages reflect real customer needs and wins, noting "Anything we learn from a customer perspective is going into marketing within the same day."
Conversation
Highlights
When Traditional Enterprise Marketing Dies: How One Founder Tripled Meeting Rates by Making Investors Do the Work
Most enterprise founders will tell you cold email works. They’ll point to their 2% conversion rates and call it a win. Charlotte Dales, CEO and Co-Founder of Inclusively, watched those same tactics fail spectacularly in 2024—and discovered something far more powerful in the process.
In a recent episode of Category Visionaries, Charlotte shared how she pivoted from traditional demand generation to a strategy that tripled weekly meeting rates and forced her team to turn off lead generation because they couldn’t handle the volume.
The Enterprise Marketing Graveyard
Charlotte’s team tried everything. “We have done demand gen, we have done webinars, we’ve done all the things BDRs, tried to do, cold calling, all the stuff,” she explains. But something fundamental had changed in enterprise sales over the past two years. “There are spam filters on every enterprise account. If you’re like attaching HubSpot tracking and stuff, it’ll just automatically decline.”
The reality hit hard. “When we first started, like I almost got a response on every cold email I sent,” Charlotte recalls. She was reaching CEOs directly with simple pitches about what she was building. “But now that everyone’s sort of able to flood people’s inboxes, at the beginning of this year were like, this isn’t working. Like we’re not getting any type of conversion. We’re spinning our wheels.”
This wasn’t a minor problem. Inclusively, which had raised $20 million and grown to about 50 enterprise clients including Salesforce and Accenture, was hitting a wall with their go-to-market motion. Traditional playbooks weren’t just underperforming—they were completely broken.
The Investor Network Hack
Charlotte’s solution came from an unexpected place: weaponizing her cap table. “I actually went to all of my investors and we have about 60 investors,” she explains. The approach was methodical and surgical.
First, she subscribed to LinkedIn Sales Navigator. Then she loaded in all 60 investors and began curating their connections against her ICP. “I would say, hey, can I have a quick 15 minutes with you? Because obviously you don’t know everyone that you’re connected to on LinkedIn. And I said, who of this list of 100 people do you actually know and will you make an intro to.”
But here’s where most founders fail—they stop at asking. Charlotte went several steps further. “We have people who write the personalized emails for each person, send them all separately, send the investor the email addresses, and then they just forwarded on with a cover letter that we’ve written.”
The results were immediate and dramatic. “We tripled our weekly meeting rates within starting that. And actually to turn it off for a while because we didn’t have enough to time to take all the meetings.”
The quality jumped too. “We’re getting higher quality introductions with way more senior people,” Charlotte notes. She didn’t stop at investors either. “I even get like my clients to do it. Like once we’re close with sort of a client or, you know, I’ll say like, hey, do you have any other chros that you know that would be interested in this?”
The Product Pivot That Changed Everything
While Charlotte’s marketing innovation grabbed immediate results, her most critical go-to-market decision happened earlier—pivoting from a hiring platform to what she calls a “retain” platform.
Inclusively started in late 2020 as a hiring solution. The timing seemed perfect. “That was like in a very good moment for DEI and where a lot of investments were getting made,” Charlotte explains. Their ICP was straightforward: VP of Talent Acquisition and Chief Diversity Officer.
But by early 2023, the ground was shifting. “The hiring market is turbulent, the DEI market is turbulent. And we need to figure out how we can actually make a sustainable impact over time that’s not reliant on strategies that will ebb and flow.”
The solution came from seeing a bigger problem. “Over 50% of people from Gen Z identify with having at least one learning difference, mental health or some sort of disability,” Charlotte points out. “And we’re already seeing the ramifications that companies processes aren’t set up. There’s 30% of people who are Gen Z get fired or leave within the first 90 days.”
The new product, Retain, allows employees to anonymously type anything about themselves—ADHD, caregiving responsibilities, divorce—and instantly see relevant company resources. “We serve up all the company’s existing products, benefits, services, technologies, policies, everything that usually is spread across a million different platforms at a company, and it’s hard to access.”
When Your ICP Completely Changes
The pivot brought a challenge most founders dread: their entire ICP changed. “It meant that it was really hard. We couldn’t just jump from our, you know, contract we had with them today to selling our new product. Cause it was a totally different buyer,” Charlotte admits.
The new buyer set was more senior—sitting under the CHRO and touching HR technology, benefits, accommodations teams. “So it’s like, you know, a catch 22,” she notes. More seniority meant better deals but longer sales cycles with more stakeholders.
Charlotte doesn’t sugarcoat the transition. “We completely had to change icps from one product to the next.” But she remains convinced it was the right move. “The problem that we’re solving now actually has a lot more bottom line impact in a positive way for organizations.”
The Salesforce Launch Strategy
Speed mattered. Charlotte and her Co-Founder leveraged their existing enterprise relationships to validate and launch Retain. “We interviewed them, we had them help us build this product,” she explains, specifically calling out Salesforce as the first pilot customer.
The timeline was aggressive. “You know, we saw this coming, built a product, got Salesforce to launch it, like all within 12 months. And we’re like, very proud of that.”
This approach of co-building with marquee customers became central to their positioning. When talking to investors, Charlotte leads with this proof point, demonstrating both product-market fit and enterprise validation simultaneously.
Tying Marketing to Delivery
One organizational decision stands out in Charlotte’s approach: tying marketing directly to customer delivery in the early stages. Her VP of Marketing reports into the service and delivery leader who manages both marketing and client-facing content.
“I think tying marketing in the early stages to part of the organization that’s actually delivering value for clients has been really helpful because those messages get so synced up,” Charlotte explains. “Anything we learn from a customer perspective is like going into marketing within the same day.”
The speed of this feedback loop shows in their results. “We came up with this new messaging around, you know, tying the macro trends to what we’re doing and really seeing like, oh my gosh, that’s like really helping people to understand what we do, the problems we solve. And you know, within a month that whole story was covered by Forbes.”
The Channel Play Ahead
Looking three to five years out, Charlotte sees strategic partnerships as the key to scaling past the enterprise sales slog. “Our big focus for this coming year is around channel partnerships and strategic partnerships,” she shares.
The rationale is simple: enterprise sales cycles are brutal. “It’s slow, it’s complex, there’s lots of people involved.” Rather than fight that reality, Charlotte wants to leverage it. “I think next three to five years I want to have two to three really strong partners that are way bigger than us in the industry that we’ve aligned to and are sort of co selling together.”
The question keeping her up at night: “What is the ICP of our strategic partnerships because those can sell so much faster for us than our sort of one off, one to one sales.”
For founders stuck in the traditional enterprise playbook, Charlotte’s journey offers a clear lesson: when the old tactics die, the answer isn’t to do them harder—it’s to completely reimagine how you create buying conversations in the first place.
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